33603-87-1

Basic information

• Product Name: 2-Propenal, 3-chloro-3-phenyl-, (Z)-
• Synonyms: (2Z)-3-Chloro-3-phenyl-2-propenal;(Z)-3-chloro-3-phenylacrylaldehyde
• CAS NO: 33603-87-1
• Molecular Formula: C₉H₇ClO
• Molecular Weight: 166.6
• Mol File: 33603-87-1.mol
• Article Data: 38

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Propenal, 3-chloro-3-phenyl-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenal, 3-chloro-3-phenyl-, (Z)-(33603-87-1)
• EPA Substance Registry System: 2-Propenal, 3-chloro-3-phenyl-, (Z)-(33603-87-1)

Safety Data

• Hazardous Substances Data: 33603-87-1(Hazardous Substances Data)

Usage

Physical State

Colorless to yellow liquid

Odor

Pungent

Primary Use

Intermediate in pharmaceutical and agrochemical production

Other Uses

Synthesis of chiral compounds, cinnamoyl derivatives, and new chemical compounds

Safety

Corrosive substance, can cause irritation to skin, eyes, and respiratory tract

Important Properties

Versatile reagent in organic chemistry, building block in synthesis of chiral compounds

Upstream product

• 536-74-3 phenylacetylene 
• 98-86-2 acetophenone 
• 68-12-2 N,N-dimethyl-formamide 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 39812-71-0 3-chloro-3-phenyl-1-prop-2-en-1-yliden-dimethyliminium perchlorate 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 1131-80-2 (E)-3-(N,N-dimethylamino)-1-phenyl-2-propen-1-one 

Downstream Products

• 62403-17-2 β-chloro-trans-cinnamaldehyde-semicarbazone 
• 3438-48-0 4-phenylpyrimidine 
• 109507-02-0 (γ-dimethylamino-cinnamylidene)-dimethyl-ammonium; chloride 
• 110422-76-9 (γ-dimethylamino-cinnamylidene)-dimethyl-ammonium; picrate 
• 69202-27-3 5-phenyl-thiophene-2-carboxylic acid anilide 
• 49571-47-3 (Z)-3-phenyl-3-thiocyanatoacrylaldehyde 
• 119858-08-1 3-phenyl-3-thiocyanatoacrylaldehyde 
• 1075-21-4 5-phenylisothiazole 
• 51000-35-2 Mercaptozimtaldehyd 
• 14597-62-7 5-phenylthiophene-2-carboxylic acid methyl ester 
• 81033-36-5 N-(1-Phenyl-3-phenylimino-1-propenyl)benzolamin 

Relevant articles and documents

Di-tert-Butyl Peroxide-Mediated Atom-Transfer Radical Addition of 2-Chlorodithiane to Aryl Alkynes under Mild Conditions

Atom transfer radical addition (ATRA) of 2-chlorodithiane onto aryl alkynes through the use of di-tert-butyl peroxide as an oxidant at room temperature directly affords a variety of synthetically valuable β-chloro-(Z)-vinyl dithianes in good yields with high regioselectivities and without the assistance of any transition metals. It provides an operationally simple pathway to access vinyl dithianes with controlled formation of a new C(sp2) - C bond and a C(sp2) - Cl bond.

MTA-Cooperative PRMT5 Inhibitors

The present invention relates to compounds that inhibit Protein Arginine N-Methyl Transferase 5 (PRMT5) activity. In particular, the present invention relates to compounds, pharmaceutical compositions and methods of use, such as methods of treating cancer using the compounds and pharmaceutical compositions of the present invention.

Pendant Alkoxy Groups on N-Aryl Substitutions Drive the Efficiency of Imidazolylidene Catalysts for Homoenolate Annulation from Enal and Aldehyde

Hydrogen-transfer in the tetrahedral intermediate generated from an imidazolylidene catalyst and α,β-unsaturated aldehyde forms a conjugated Breslow intermediate. This is a critical step affecting the efficiency of the NHC-catalyzed γ-butyrolactone formation via homoenolate addition to aryl aldehydes. A novel type of imidazolylidene catalyst with pendant alkoxy groups on the ortho-N-aryl groups is described. Catalyst of this sort facilitates the formation of the conjugated Breslow intermediate. Studies of the rate constants for homoenolate annulation affording γ-butyrolactones, reveal that introduction of the oxygen atoms in the appropriate position of the N-aryl substituents can increase the efficiency of imidazolylidene catalysts. Structural and mechanistic studies revealed that pendant alkoxy groups can be located close to the proton of the tetrahedral intermediate, thereby facilitating the proton transfer.